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TCI Practical Example: Cross-Coupling Reaction Using Palladium on Carbon

We are proud to present the Suzuki-Miyaura cross-coupling reaction of 4-chlorobenzotrifluoride and phenylboronic acid using palladium on carbon as a catalyst. Palladium on carbon can be removed by filtration.

Used Chemicals

• 4-Chlorobenzotrifluoride [C0305]
• Phenylboronic Acid [B0857]
• Palladium 10% on Carbon (= Pd/C) [P1785]
• Potassium Carbonate (=K₂CO₃) [P1748]
• N,N-Dimethylacetamide (= DMA)

Procedure

4-Chlorobenzotrifluoride (500 mg, 2.77 mmol), phenylboronic acid (506 mg, 4.15 mmol), palladium on carbon (14.7 mg) and potassium carbonate (765 mg, 5.54 mmol) were dissolved in DMA/water (4.5 mL/0.5 mL) and stirred at 80 °C for 24 hours. The reaction mixture was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 0:100 - 5:95) to give 4-(trifluoromethyl)-1,1'-biphenyl as a white solid (485 mg, 79% yield).

Experimenter's Comments

The reaction mixture was monitored by UPLC.

Analytical Data

4-(Trifluoromethyl)-1,1'-biphenyl

¹H NMR (270 MHz, CDCl₃); δ 7.60-7.54 (m, 4H), 7.49-7.46 (m, 3H), 7.41-7.36 (m, 2H).

Lead Reference

• Activation of Aryl Chlorides for Suzuki Cross-Coupling by Ligandless, Heterogeneous Palladium
  • C. R. LeBlond, A. T. Andrews, Y. Sun, J. R. Sowa, Org. Lett. 2001, 3, 1555.